Dealbreaker: He Has Low Self-Esteem

The night we met, he grabbed my hand and told me my name was beautiful. My heart jumped a little, and I’m not even into corny stuff like that. He was confident, cuddly, edgy—like some kind of bad boy teddy bear you want to hug and kiss and do all that other fun stuff with. This was not my usual type.

I gave him my number. He texted me. We began to formulate plans to meet. Then, he treated me to months of back-and-forth texts, a handful of dates, and a raft of halfhearted excuses. One was recurring: He had recently lost his job, he said, and felt wrong trying to date a woman like me until he had enough money to “come correct”—take charge, foot the bill, feel like a man.

I didn’t realize it at the time, but he was actually exactly my type. It’s taken me many failed first dates and as many broken relationships to figure it out: I attract and am attracted to men with low self-esteem (MWLSE).

By MWLSE, I don’t mean dudes who are a little bit insecure. We all get a little insecure from time to time. I mean men who are so bogged down by their warped vision of themselves that it haunts every aspect of their being.

In retrospect, I should have known I was dealing with a MWLSE. Instead, I swallowed his lines and tried to look at the positives, even if that meant making them up. He recognizes that I’m almost too incredible for him to handle. It’s about time someone figured that out, right?

At the time, I was busy running a major feminist website, keynoting multiple conferences, and penning my first book about dating, love, and feminism. At first, he was intrigued (“I’m so impressed with how successful you are”). But his feelings toward my work quickly devolved into insecurity (“you realize I’m a loser, right?”) and finally, passive-aggressive digs (“Why is it that I seem to be acutely aware of your success?”).

Despite the vigor with which he was waving his red flags, I put my professional feminism to work in locating a political justification for his behavior. Unfair standards of masculinity, I told myself, put undue pressure on men to be “men.” As a feminist, I recognized that when men don’t act man enough, their girlfriends, friends, and families can disapprove. The pressure can be devastating. And those unrealistic expectations of manhood are only exacerbated by a broken economy. How could I not be sympathetic?

Obscured by my righteous political justification was a far less feminist lining—the kind where he hurts me, and I let him. He chose to deal with his very real identity crisis by wielding his anxious masculinity at every turn in our relationship. I cut him slack for his insecurity, and he used every inch: He was mysterious, unreliable, withdrawn.

The most troubling side effect of this behavior was that I began to downplay my own successes. All of a sudden, it wasn’t that he was insecure—it was that my success had inadvertently caused his condition. I went from sharing my excitement about everything that was going on for me to telling him that my success was new, scary, some sort of fluke. I avoided talking about how much I had hustled to get where I am. But my accomplishments could never be minimized enough. The more things got better for me, the more insecure he became.

I wasn’t the only one drawing this crooked but convincing line between my success and his failure. I couldn’t open up any newspaper or lifestyle website without reading another story about how successful women have killed romance by making our male partners feel bad about themselves. The solution? We should stop being good at stuff, or at least stop talking about it. Only then could we find men who were free to be truly confident, unhampered by the weight of our accomplishments.

In the end, those stories were right about one thing. After all of my waiting and hoping, he broke it off with me because he had found another woman he wanted to pursue more seriously. I was left to wonder how exactly a MWLSE finds the balls to pursue a relationship with someone else.

This wasn’t just a slap in the face: It was a wake-up call. My bigger problem was not this man’s insecurity, but my own. I had internalized the belief that strong women scare men, and I was compensating for my big, bad success by doling out chance after chance after chance. And I’m hardly the only one who's had trouble letting go. Our whole culture remains wedded to an outdated idea of gender relations that stacks the deck against our happiness.

A few months ago, I heard from my MWLSE again. He was now employed, he said, and was interested in reconnecting. I’m confident that with time, our society is capable of reversing its course on traditional gender roles. But it's not going to come with a MWLSE finding a job that allows him to reassume his tough-guy posture.

As for me, I’m learning to recognize the signs of a MWLSE before the cycle repeats itself again. Has this led to me finding a guy who can hold his own in a relationship? Frankly, no. But it has made me happier and more confident in myself—confident enough never to settle for someone who isn't.